Most hobbies are not circumstantial. Crossdressing is not most hobbies.

For the new few days my girlfriend’s mother is visiting and staying with us. This, unfortunately, puts crossdressing on the shelf for a weekend. Absence makes the heart grow fonder.

More pictures on Flickr....

More pics available on Flickr…

Here are some positive I will focus on to make the weekend go by faster. (In all likelihood, focusing on these things will actually slow the weekend to a grinding halt.)

1) Gorilla masking tape is the best cleavage creator, hands down.

2) I will be shaving my legs for the month of October – exciting!

3) When the weekend is over, it is the month of Halloween (also known as Chrosdressermas.)

4. I ordered four new pairs of shoes on Payless. They had a buy one, get one half price deal. I took advantage of it twice. (Heads up, if you ever buy shoes from Payless online do a Google search for “payless coupons” and you’re very likely to find some nice 20%-off codes.) I will gleefully post pictures of all my shoes when they arrive.

So, until Monday night, the heels are in the closet and the wig is on the shelf. Time to man up!


Here’s something!

Want to see all of the photos from my blog unblurred, plus some other photos?

Just friend me on Flickr, located here. I’ll try to accept as quickly as possible. I know it seems kind of dumb, maybe even a little bit patronizing, but I will remind you, I probably shouldn’t risk posting unblurred photos in the open. This will have to do for now. Ask me again about it June 2014.

Meanwhile….. I’m dressed now… I didn’t plan on it…. but I had the house to myself for a few hours. These things just kind of happen. Oh well!

(edit – note: you have to be signed in to your account to add a contact.)

Who Am I?

When you discuss the word “identity” in terms of crossdressing there are two ways to look at it.

1) The identity of the male, as the crossdresser, and what it means to him – how he will adjust to/deal with/understand  his identity as a crossdresser.

2) The identity of the crossdresser en femme – how he sees her, who she is, and how she sees herself.

They say the difference between an experienced teacher and an inexperienced teacher is the question they ask themselves at the end of the day. The inexperienced teacher says, “How am I doing?” and the inexperienced says, “How are my students doing?”

As a new crossdresser, in regards to my relatively recent outness, I’ve been focusing in my blog primarily on the first interpretation – which I believe corresponds to the “How am I doing?” question. Now, with some experience under my belt, it’s time to focus on her.

My girlfriend once asked me if Justine had her own personality.

She had noticed that I was more “cuddly” as Justine – more willing to touch and be touched. En homme I’m not one for touchy-feely. I don’t think I’m cold or aloof – I’m just never the one to embrace embraces. As Justine it is the opposite – sometimes it almost seems as if I crave the presence of others. I think this is definite remnant of when crossdressing served primarily as a fetish. Touching is primal and sexual, and when I am crossdressing those feelings are certainly present in my mind.

So yes, in that aspect – I, Justine, have my own personality. In thinking more about the subject – it is, however, deeper than I initially imagined. (I’m beginning to believe that all of crossdressing is deeper than I imagined, but that’s just another thing I love about it.)

Something I wish I could do, but never do, is dance. I spent three years in college going to bars where other people danced around me. I’ve gone to numerous weddings, bar mitzvahs and other parties where I sit sheepishly and watch others have a good time. There’s something about an awkward white guy that screams, “DO NOT DANCE!” I don’t know if it’s a case of societal stereotypes breeding self-fulfilling prophecy, or just that the genes for science fiction fanaticism and lack of rhythm go hand-in-hand. When I’m Justine, though, I want to dance. I want to be able to go out and have a good time in a way that the male me doesn’t (or can’t?) I want to be who I am not in a way that goes beyond gender.

In My Husband Betty, Helen Boyd discusses how, often, crossdressers’ female selves are often representative of the female they desire. Discussing this is treading on dangerous waters because a) I have a girlfriend and b) until now I have not thought of myself as this type of crossdresser.

I want to be very clear here – I love my girlfriend and want to be with her. When I crossdress, Justine, in a fictional way, is another girl I desire. Despite the fact that a television show called, “The New Adventures of Justine” would consist of sitting on the couch watching movies, typing blog posts, episode after episode, I fictionalize an entire backstory for her (or me) that has never existed. I imagine Justine (me) goes out and has a good time, rebuffs the pick-up lines of men, and knows her way around the world in a way that the male me does not. She is calm, cool and a little bit kick-ass. She is interested in the same things I am, but is more confident. Despite all this, she would still be into a guy like me. In a way, I am in love with myself.

I need a cool theme song...

A Crossdressing Sitcom


It’s funny, though, because all of those things that I described Justine as? That’s also how I think of my actual girlfriend. What doesn’t make sense now, is why does Justine exist? I have always had very low self-confidence in my male form – creating Justine, I reiterate and believe, allows me to be who I am not. It just so happens that she is what I believe a girlfriend should be/who my actual girlfriend is.

This tells me one thing: The girl of my dreams is nearly identical to my girlfriend. This is a good thing.

This also begs the question: Does Justine need to exist if I am content in my relationship? The answer is yes – and I think Justine would exist in the very same manner she does now, regardless of my relationship status. I don’t view Justine as a replacement girlfriend, but as a version of me that the male me desires – even if most people meet that quota in their ideal relationship.

I’ve digressed, now. This blog post was originally intended to describe Justine – not question of her (my) place in my (his) life. I suppose that understanding the relationship between Justine, male me, and my girlfriend is related, however – because in some ways this is a monogamous relationship with a third “heel.”

So I’ve now defined Justine in terms of existance, but the personality question still lingers. I can tell you this (and it may be redundant.) Justine is fun, happier, and in my head more outgoing than male me is. She likes fashion, sci-fi, shopping, board games, partying, and cuddling at night. She is a more wholly realized version of me. The aspects of me that have been repressed for one reason or another (that’s a whole ‘nother post…) She likes to be dominated, but also sometimes do the dominating. She likes to take you by surprise just as much as she likes to be surprised. She is me, but she is not. Her and I are me, and they are two sides to the same coin. (Wow, talk about cliche.)

This has been a very healthy blog post. I started writing it, not knowing where it would end up, and I am very happy with the results. My mind is clearer about my identity, and perhaps that mental first step is part of the path to a physical first step out the door. I wanted to go for a walk outside tonight with my girlfriend, but I used the rain as an excuse. There are about five perfectly good umbrellas within fifteen feet of me. I’m lame. One day.




I enjoy looking at the various search terms people use that eventually lead them to this blog. Today’s “Rossdresser” was one of my favorites.

I have to imagine rossdressing involves dressing up as Ross Geller from Friends. There is also the less popular rossdressing alternative, which is when you have an indescribable desire to emulate Ross Perot. To each his (or her) own, I suppose. Personally I’d rather dress like Monica.

My two FreeBra replacements arrived today – I expect some new photos this weekend. For now, this should tide everyone over.

Pretty creepy

Wow. This is scary.

Alright. Not even I’m going to deny how creepy this is. Sweet dreams, everyone! 🙂

Steppin’ Out

Time to exhale. It’s been a very busy four days and now finally this evening I’m dressed up for the first time in over a week. It feels good, relaxing. I’m trying a technique to slim my eye brows using white eye liner and a small concealer brush. From a distance it works pretty well, but the illusion is ruined up close. Practice makes perfect.

The real reason for this post, though, is not my thick eyebrows, (which, to be quite honest, I could wax poetic about – negatively of course.) I write, tonight, because I feel like I have hit a wall – or a door, if you’re going to be literal.

I’ve been dressing up, with mild success, for just about two months now. I’ve purchased new things. Told new people. Experienced new feelings. I think, however, that I have hit a plateau. What else is there to do? Where is there to go? The answer, is simple – outside.

An outdoor excursion is perhaps even scarier than coming out of the crossdresser closet. When I told my girlfriend and subsequently some of my friends, I was in control. I knew who I would be talking to. I could gauge their reactions, predict what they might say, and terminate the event in case of an emergency.

Leaving the confines of my house is a completely opposite experience. The only thing in my control? Me. Every person I pass by, in my head, is a coin flip – will they react or won’t they. I’m only concerned about negative reactions – and not in the “you’ve been read” sense, but the name-calling, violent-acting sense. I can handle stares, I just don’t want to put myself in danger.

I realize, yes, I live in New York City, the liberal-mecca of the world – but that is a stereotype, like any other. There are people you want to avoid here if you’re crossdressing, and neighborhoods you probably want to stay out of.

One of the things I do have some control over is setting. Only in terms of destination however. I’ve done some research on bars in NYC that would be accepting of crossdressers, and also meet the criterion of what I’m looking for. I want a bar that is LGBT-friendly, low-key, non-dancey and would also be welcoming of a few friends, since I would like my first time out to be with a group. I don’t want to have to travel too far by subway. I only live two stops away from Manhattan, but it’s quite a bit farther if I want to go to the more LGBT-friendly west village.

I think it would be wise if I took some small steps, before great bounds. I want to take a walk around my block. I want to walk over to a friends apartment. Little victories that boost confidence towards larger ones. I need to keep telling people I’m going to go out, and keep telling myself.

In order to talk myself up, I think it would be prudent if I listed my fears, what I think will happen, and what will probably actually happen.


My Imagination

Probable Reality

Recognized by landlord or neighbors on way out of house Kicked out of apartment, tormented by neighbors It will be dark out and no one will see.
Harassed on subway Called names/assaulted by intolerant jerk No one will say anything. Who talks to people on the subway?
Bad bar experience Bar patrons are jerks because I’m the T part of LGBT. No one will care. I will complain about price of beer.
Long subway wait back at night in shady area. Train doesn’t come for hours and I’m drunk and stupid. I can take a taxi.

Alright. I feel a little bit better after writing that. I have to focus on the realistic. Focus on the positive. I am a crossdresser, with an accepting girlfriend and friends, and may be slightly passable enough to go out for a few drinks. That needs to be my mantra.

If anyone reading this has any suggestions, tips or pointers about going out let me know. Whether it’s a certain attitude to take, or places to go in NYC. I’m all ears.

On a less serious note, I’ve been marathoning Doctor Who, and would like to dress up like Amy Pond. Minus the red hair. That is all.


Hello, Internet. I’ve been avoiding you. No – not really. Just very busy.

Work has started and is in full swing, and like I predicted earlier, there would be less time for Justine than in those wonderful summer months. My intent for the weekend was to come home from work, relax, blog and then probably dress up on Saturday – I wouldn’t be so exhausted. Plans change in an instant, sometimes.

My grandfather passed away this morning – this was quite expected, but I am still very sad. I don’t want to dwell on this in this blog, however I will touch upon it as it is slightly relevant. Initially, and perhaps selfishly, I thought about how this now wouldn’t be a good weekend for crossdressing. Who wants to dress up when they’re sad? Crossdressing is a happy experience, not to be marred with death. I’ve thought about those early sentiments, though, and decided that if crossdressing is to be part of my life, it will be so no matter the circumstance. I should be able to dress up and blog – I don’t stop any other habits for a death in the family. I can pay my respects and still dress up on my own time.

In an odd way, I also think that my grandpa might have been supportive, or at least okay with my crossdressing. When my siblings and I were little, he would whoosh us away from family gatherings and dress us up in ridiculous outfits to make everyone else laugh. I don’t think he ever had any of us crossdressed, but he was certainly a fan of the avant garde.

I wanted to write a post today about my crossdressing routine. In My Husband Betty, Helen Boyd mentions that her husband, at least the the beginning of his crossdressing, adhered to a strict “routine” – that is – crossdressing preparation and processed in a certain order. I don’t know about other crossdressers, but I certainly have a routine that I follow, and I’m curious to know if it’s anything like what other girls do.

0a. Shower – If I’m dirty or it’s been a long day a shower beforehand is always a good idea.

0b. Shave chest – only if I’m going to be wearing something low cut…. which nowadays I usually am.

1. Shave face – I like to shave before I do anything else. Once I’m dressed up, I don’t want to risk getting shaving cream on any clothes.

2. Tuck – Initially I hated tucking – I couldn’t do it very well and it was uncomfortable. Over time I’ve gotten better at it. Now it only takes quick second and I don’t even notice it. I use a gaff after tucking to keep everything in place securely.

3. Hip/Rear pads – self explanatory, I think.

4. Waist cincher – Last Halloween I dressed up as a hipster chick – this was before I was out to anyone. Before I chose hipster chick, my original idea was to dress as my girlfriend – which gave me the leeway to buy cheap butt pads. The pads were part of a waist cincher that worked amazingly well – better than the pads, actually. After buying nice pads, I cut the padding off of the old Halloween pair, so I could still use the cincher. Works great.

5. Spanx – this is a fairly new edition, but I sometimes like to use spanx that go from my upper tight to my waist. It smooths over everything else underneath.

6. Underwear – Probably not necessary after the aforementioned layers, but a favorite I wouldn’t give up.

7a. Freebra (if I want cleavage)

7b. Breast forms

8. Dressing up – I used to put on my make up before I got dressed. This was a terrible idea as I ruined collar after collar putting on shirts with a made up face. My girlfriend wisely suggested that I dress up first, and then do make up. Brilliant.

9. Make up – applied in the following order: concealer, foundation, powder, blush, eyeliner, eye shadow, mascara, lip stick/gloss.

10. Jewelery – usually earrings and a necklace.

11. Wig – the finishing touch, which I believe adds more to the illusion than anything else. The icing on the cake, I suppose.

So yes, you could call me meticulous. What can I say? If it works, don’t try to fix it. There are, of course, minor things that change from time to time – but this is pretty much how it goes. Also note that following dressing up, I usually wind up preening for way too long. It’s funny, because in guy mode I couldn’t care less about preening, but I suppose that’s how it is when you’re a crossdresser.

As the ocean ripples filter across my face.

From a few weeks ago

I think, after finishing writing, that blogging was a good idea.  It got my mind of things for a bit, and just the idea that I can semi-openly blog about crossdressing is a happy thing. I haven’t dressed up in about a week now, unfortunately, but I will leave you all with a picture from a few weeks ago until there is time for another dressing.



Well, I’ve hit a new level. I never thought this would happen.

I’m writing this, fully dressed, make-up, breasts, clothes – you name it. But I’m grumpy.

Back in the beginning of July if you had told me that I would be able to crossdress, look pretty decent, all while my girlfriend was home I would have told you two things:

1. Shut the fuck up.

2. Seriously? Oh – then that’s the best thing in the world. Nothing can ruin that.

It’s September now, though, and I’ve been dressing for about two months. Each time adding a little more, getting a bit better, and more comfortable. Except now I’m grumpy.

This is me, slightly grumpy

Slightly grumpy.

While dressing tonight my FreeBra broke. Yes, I know – it’s a piece of garbage. I spent a few bucks on it, and even in my last post I thought it’s durability was questionable. Here’s the thing, though. It’s still adhesive, but the silicone gel broke. The left boob just split. While I was dressing. And I looked pretty good, to boot.

Jump to the present. I’m still dressed, my cleavage is minimal, and now I know that I have spent enough crossdressing that I can be grumpy while doing so. The endless euphoria an uncloseted crossdresser feels comes with a caveat. It ends.

Don’t get me wrong. I’m still happy to be dressed. I imagine this is how a genetic girl feels when a favorite bra breaks. My cleavage – gone, just like that!

In an effort to play the optimist, I’ll try to look at this from another angle. I’m comfortable enough crossdressing that it no longer feels like an experience, and it’s just another part of life. That’s really cool – crossdressing is the new normal. That’s something to celebrate. The fact that I can type a blog entry, watch the Mets game, or read a book, forgetting the fact that I’m en femme is awesome.

Before I came out, any time I tried to do these things while home alone and dressed, I couldn’t pay attention. Every sensation was too new, too exciting. Now I can compartmentalize and enjoy being dressed while not even realizing it.

So I take the good with the bad. No cleavage, but the ability to relax, breathe and be me. Besides, I shouldn’t be grumpy. I ordered two more FreeBras from ebay. Next time I’ll be prepared!

In other news, my girlfriend braided my hair earlier. I think it looked pretty good, but I prefer to have my hair hide the sides of my face – I think it makes me look less masculine. It was fun to try, though, and looked cute with my outfit.

Also to note – I had 91 hits the other day, and over 100 during a 24-hour span. That’s pretty damn cool. A number of different countries, too…. So hello anyone actually reading this!

Cleavage! (Part Deux)

Multiple angles

Using the “Freebra”

So yesterday the FreeBra arrived in the mail, which I saw after watching the tutorial on YouTube, originally posted by Emsy. I didn’t follow the instructions exactly, choosing to use only one FreeBra, combined with my breast forms and pocketed bra.

The results, you can see, look much better than the make-up born cleavage – and it also takes much less time. The FreeBra forms (or at least the Chinese knock-offs I have) have a sticky backing that when it arrives is protected by plastic. After wearing the forms for a few hours they started to shift a bit due to sweat. When I removed them they were not as sticky as when they arrived, which I suppose is to be expected.

I washed them gently with some soap and water, which will hopefully preserve their stickiness, but if not, they’re very cheap on ebay and if needed I can order another set (or two!)

After wearing them, by the end of the night, my neck hurt from looking down so much. I honestly couldn’t believe how well they worked. Even my girlfriend, who was shocked when she saw them, was caught staring a few times. Society has raised everyone, regardless of gender, to have a built in cleavage detector.

Please note that if the pictures don’t look the greatest, it’s because I didn’t fully dress up to try this out, so obviously no wig, my chest was not 100% shaved, and some red marks from the first shave are also visible. This weekend I hope to be able to put everything together to see how it looks completed.

I still want to do an in-depth Halloween post, discussing what Halloween means to me as a crossdresser, what it might mean for closeted crossdressers and their families, and then a full pictorial breakdown of my “costume.” I will probably, wait til at least October to post it though, so to be more in the spirit when the spirit is in fact in the air.

The Internet is for…

I’ve been delaying writing a post about the internet since I started writing this blog last month. This is partially because I feel like it is going to be a long post, and I don’t like writing long posts. My delay is also due to the fact that there are some aspects of my internet-related crossdressing experiences that I am hesitant to reveal, but alas, probably will anyway.

When I first started to delve into crossdressing I did not realize the breadth of information the internet had to offer. Somehow – I don’t remember how exactly – I wound up on StorySite.org. For those uninitiated, or unwilling to click, it is essentially user-submitted trans-fiction.

I think it is imoportant and telling that I stumbled upon crossdressing fiction before any photo or personal sites. Fiction, or text in general, I think, was a good ease in to the crossdressing world. As a thirteen year old crossdresser-in-training I was afraid of my hobby – what it was and what it meant. Reading something, in my mind, was certainly less deviant than looking at something, or doing something. This was a double-edged sword, however. Yes, I wasn’t actually looking at anyone crossdressing, but I was instead expanding my crossdressing vocabulary and imagination in ways a photography couldn’t possibly.

Different Blur Filter

Not seizing, just blurred again

I gravitated towards one author, Janet L. Stickney. I have no idea who Janet actually is, or if I should actually be writing, “Janet.” What I do know was that at the time these were my favorite stories because often times I wished I was the main character. Reluctant, but not forced, feminization. Young boys accidentally finding themselves in situations where their families or friends would help them dress up for social situations – and lo and behold – every time they were beautiful!  Having re-read a number of these stories recently out of curiosity I now see how repetitive and simple they are. Often times the characters have easy-outs of situations, but choose to ignore them. Most of the characters at some point realize they like dressing up, and after some denial, eventually embrace it – much like the readers.

Reading these stories allowed me to live vicariously through the characters and provided a safe outlet for a young crossdresser. I realize there are many other types of trans-fiction – forced feminization, rape stories, etc. I’ve read some of them, experimentally, but they’re not for me. Just like every crossdresser has his own unique crossdressed self, fiction tastes are equally different.

I don’t think I’m alone in my evolution of internet-related crossdressing content. When I stopped secretly dressing up in my mother’s clothes around eleventh grade my interest in fiction started to become an interest in pictures. First, crossplay.

I was always very careful about keeping my computer clean – that is – constantly deleting history, cookies and caches. My StorySite visits almost always happened on the family computer when nobody was home or in the room. It is no coincidence then that my interest in photographs and pictures began at the same time I got an internet connection in my room. Despite my computer cleanliness I think crossplay was easier for me to look at because I felt I could justify it. “Oh, I was just looking at a section of a cosplay site” is a lot easier to explain than looking at pictures of crossdressers. The cosplay.com forums were a popular place for me to lurk. Especially the “Can I Pass?” threads where people would post pictures and ask for opinions.

I loved looking at pictures of people who were bold enough to dress up. Comfortable enough to talk about it with somebody, even if was just online. To this day I remember the first time I took my interest in photographs to another level.

Even though I was always aroused by reading StorySite, I never masturbated to it. After reading, I would always pull up a tradition pornographic photo and masturbate to that instead. I was guilty about being turned on by crossdressing. Looking at photos was no different. Yes, I am straight, but crossdressing and henceforth, crossdressers, are a turn on. One night I decided to keep the photograph of a crossplayer open in a tab behind my regular material. Overtime, I stopped trying to justify it and the tabs stopped.

I don’t know if I should feel guilty. There are a few things I could feel guilty about.

Is masturbating to the anything crossdressing-related wrong? No, I don’t think so – there’s nothing to be ashamed about with a fetish – especially when you’re a teenager and first discovering your body.

Is masturbating to pictures of crossdressers wrong? I don’t know. I’ve had this debate before with people – just change the question to be about pictures of people on Facebook.

I try to justify it by explaining that nothing is actually happening to the people in the photographs. They have no idea what their photographs are being used for, so it really shouldn’t affect them. If a real girl uploads a photograph of herself in a bikini and a guy masturbates to it – did he do something wrong? The girl doesn’t know about it, the guy is happy, and everyone moves on with their lives. It’s a tricky area and to this day I still don’t know what is right.

Moving on – Cosplay.com eventually became more websites. Crossplay.com was a popular destination, along with countless blogs. Jessica Spirit, Aubrey Frost, Sarah Myles and more. Unfortunately, many of these sites are no longer with us.

Eventually Flickr came along and opened me up to thousands of other wonderful crossdressers. YouTube was, and still is wonderful. JayeKayeTV, to this today, maintains an amazing favorites list of the best crossdressing videos online. Make-up tutorials, before and after videos, music videos, performances and more. JayeKayeTV’s channel has probably been more motivating for me as a crossdresser than another website. It also made me wish Japanese game shows caught on in America (not just Ninja Warrior.)

Today there are a number of wonderful crossdressers online. The bloggers and websites that I follow today, and I wish were around when I was younger include Jessica Who, Gabreilla Hermosa and Elizabeth of MyWeekendShoes. I also lurk on the crossdressing subredit, with the aspiration to eventually either post a picture or a link to this blog.

So there’s that. Wow. I feel like the end of this post was a bit rushed – maybe I’ll elaborate on it more later. Either way, I have to wonder if my experiences mirror those of other crossdressers. Lately I am anxious to talk to other CDs – be part of a community. I would like, one day, to at least be friendly with other CDs. Lurking online is not the same as taking part in constructive conversations.